Tempo

Base Information

• Chemical Name: Tempo
• CAS No.: 2564-83-2
• Deprecated CAS: 25657-03-8,125012-91-1,126517-51-9,26933-82-4,54637-06-8,64104-42-3,1357396-80-5,125012-91-1,126517-51-9,1357396-80-5,26933-82-4,54637-06-8,64104-42-3
• Molecular Formula: C9H18NO
• Molecular Weight: 158.264
• Hs Code.: 29333999
• European Community (EC) Number: 219-888-8
• UNII: VQN7359ICQ
• DSSTox Substance ID: DTXSID2073300
• Nikkaji Number: J2.763.954B,J100.807B
• Wikipedia: TEMPO
• ChEMBL ID: CHEMBL606971
• Mol file: 2564-83-2.mol

Synonyms:2,2,6,6-tetramethyl-1-piperidinyloxyl;2,2,6,6-tetramethyl-4-piperidine-N-oxide;2,2,6,6-tetramethylpiperidine-1-oxyl;oxoammonium TPO;TEMPO

Chemical Property of Tempo

Chemical Property:

• Appearance/Colour: orange crystals or powder
• Vapor Pressure: 0.4 hPa (20 °C)
• Melting Point: 36-38 °C(lit.)
• Refractive Index: 1.4350 (estimate)
• Boiling Point: 193 °C
• Flash Point: 154 °F
• PSA: 3.24000
• Density: 1 g/cm³
• LogP: 2.31290
• Storage Temp.: 2-8°C
• Solubility.: 9.7g/l
• Water Solubility.: Soluble in all organic solvents. Insoluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 156.138839198
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

2,2,6,6-Tetramethylpiperidine 1-oxyl, free radical, free flowing milled solid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amine Oxides
• Canonical SMILES: CC1(CCCC(N1[O])(C)C)C
• Uses: TEMPO(2,2,6,6-Tetramethylpiperidinooxy) is a stable radical prepared through the oxidation of 2,2,6,6-tetramethylpiperidine. TEMPO has a wide range of applications including use as a free radical scavenger, a reagent in organic synthe sis and as a structural probe in electron spin resonance spectroscopy. TEMPO can also be used as a mediator in free radical polymerization. In organic chemistry as a radical trap, 2,2,6,6-Tetramethylpiperidinooxy can be used as a catalyst and in polymerization mediation. TEMPO can be used:As a catalytic oxidant for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.As a catalytic oxidant in the iodobenzene diacetae oxidation of nerol to neral.For trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene. In the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air

Technology Process of Tempo

There total 80 articles about Tempo which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate + N-fluorobis(benzenesulfon)imide (133745-75-2) → 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + dibenzenesulfonamide (2618-96-4)

Guidance literature:

With 1,1,1,2,2,2-hexamethyldisilane; copper(l) chloride; In acetonitrile; at 70 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tetlet.2017.01.015

Reference yield: 96.0%

2,2,6,6-tetramethyl-piperidine (768-66-1) → 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3)

Guidance literature:

With dihydrogen peroxide; potassium carbonate; In dichloromethane; water; at 20 ℃; for 6h; pH=10;

Reference yield: 92.0%

2,2,6,6-tetramethylpiperidin-1-ol (7031-93-8) → 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3)

Guidance literature:

With N,N,N',N'',N'''-pentamethyldiethylenetriamine; copper; copper(I) bromide; In benzene; at 60 ℃; for 0.5h; Inert atmosphere;

DOI:10.1246/BCSJ.20200398

upstream raw materials:

2,2,6,6-tetramethyl-piperidine

1-benzoyl-2,3-di-indol-3-yl-1,2,3,4-tetrahydro-quinoxaline

2,2,6,6-tetramethylpiperidin-1-ol

2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride

Downstream raw materials:

1,5-cis,cis-cyclooctadiene

S-(+)-1,2-trans-2,9-trans-9,10-trans-tricyclo-<8.6.0.0^2,9>hexadeca-cis-5-cis-13-diene

1,2-cis-2,9-trans-9,10-cis-tricyclo-<8.6.0.0^2,9>hexadeca-cis-5-cis-13-diene

1,2-cis-9,10-trans-tricyclo-<8.6.0.0^2,9>hexadeca-cis-5-cis-13-diene

Refernces

• 1、 Kagan,Yanilkin,Morozov,Nastapova,Zhukova,Kashparov,Kashparova. "Mechanism of electrochemical oxidation of 1-chloro-2,2,6,6- tetramethylpiperidine". . p. 1001 - 1003. Retrieved 2009.
• 2、 -. "Method for preparing hindered amine nitroxide free radical compound by alkaline heterogeneous catalysis system". Paragraph 0050-0053; 0058-0059. . Retrieved 2021/09/26.
• 3、 Waggoner, Abygail R.,Abdulrahman, Yahya,Iverson, Alexis J.,Gibson, Ethan P.,Buckles, Mark A.,Poole, James S.. "Reaction of hydroxyl radical with arenes in solution—On the importance of benzylic hydrogen abstraction". . . Retrieved 2021/08/27.